Multi-step reaction with 11 steps
1.1: dimethyl sulfoxide / 0.08 h / 20 °C / Inert atmosphere
2.1: pyridine; dmap / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere
3.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere
4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 4 °C / Inert atmosphere
6.1: bismuth(lll) trifluoromethanesulfonate / dichloromethane / 1 h / -15 °C / Molecular sieve; Inert atmosphere
7.1: ozone / dichloromethane / 0.03 h / -78 °C
7.2: 0.25 h / 0 °C / Inert atmosphere
8.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
9.1: palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C
10.1: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 42 h / 20 °C / Inert atmosphere
11.1: boron tribromide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
11.2: Inert atmosphere
With
bismuth(lll) trifluoromethanesulfonate; pyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; nickel(II) chloride hexahydrate; trimethylsilyl trifluoromethanesulfonate; palladium on activated charcoal; tetrabutyl ammonium fluoride; hydrogen; boron tribromide; sodium hydrogencarbonate; ozone; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide;
4.1: Suzuki-Miyaura coupling / 8.1: Wittig reaction;
DOI:10.1016/j.tet.2011.09.033